


Green-Eyed Cowboy

by Silent_Chick



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - College/University, Caring Dean, Confident Dean, Crushes, Dean to the Rescue, Embarrassment, F/M, Original Character(s), Original Female Character(s) - Freeform, Reader-Insert, Sweet Dean Winchester, sprained ankle
Language: English
Status: Completed
Published: 2017-06-18
Updated: 2017-07-12
Packaged: 2018-11-15 12:46:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,756
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11231295
Author URL: https://archiveofourown.org/users/Silent_Chick/pseuds/Silent_Chick
Summary: You're on your way to the bus stop, only problem is... you just sprained your ankle.





	1. Chapter 1

Finished with class, you were on your way out of the building. You had to catch the bus, but there’s time to kill before you get there.

In no rush, you let your mind wonder. It was Monday and you had the week off. It hasn’t been busy at the diner, so you’re glad your parents help you out financially.

Your phone goes off and you pull it out to see who it is. It’s your friend Amanda. The two of you were supposed to go out for pizza, but you kind of wanted to go to a buffet. You put the phone back in your pocket.

Saying thanks to a guy that opens a door for you, you lollygag on the path.

Not too many people are here today. From what you heard, some classes were cancelled today. Too bad it wasn’t yours.

There was a group of girls and guys, talking to one another. Two had backpacks, four had one earbud in, two had books in their arms, and one didn’t have anything.

One of the guys were talking, he had really deep blue eyes and dark brown hair.

You knew you were staring at them, but you weren’t really staring at them. You were observing them. It sounds weird, but usually everyone is rushing to class and they don’t spend time to just hangout and talk like it was high school. It isn’t high school, but it’s sometimes nice to have reminders of the good times.

That and a guy you and Amanda stare at constantly, anytime you get to see him, is in the group. He was one of the ones with an earbud in.

He’s nodded to you before and you almost tripped because you were going down the stairs. It was a few weeks before Amanda let that go.

Pulling out your phone, the bus is about to come in a few minutes. So, you start your journey.

Strolling your way down the path, you have your hands in your hoodie pocket. You’re planning to start on your work as soon as you get home, so you don’t have to worry about it. Moving your shoulders to adjust your backpack, your foot hits something. It wouldn’t be a problem, if that something didn’t make you fall.

There was a crack in the path and you didn’t lift your foot enough to avoid it.

You lay there on your side, highly embarrassed because you hear a bunch of high pitched laughter. Of course, you fell in view of the group and other people passing.

Making a move to get up, you move your foot, only for a sharp pain to rip through your ankle.

You feel hands land on you lightly.

“You okay?”

_Shit, it’s Green-Eyed Cowboy._

“Yeah, I’m fine. Thank you.”

He looks doubtful. He gets up, pulling you off the ground. You suck in some air, reminded of the pain in your ankle.

You look at his group and the girls are laughing while the guys look slightly concerned.

“Are you okay!?!” The one with the deep blue eyes asks.

“Yes, thanks!”

The guys seem satisfied.

“Where were you headed?”

“To the bus stop, but I think I’m gonna head to the nurse now.”

“You fine to walk by yourself?”

 _No._ “Yeah, I got it. Thanks.”

He nods turning to go back to his group. You bite your lip, balling up your fists in pain with each baby step you take. You took at least four baby steps before you had to stop.

On the verge crying from embarrassment and pain, you pull out your phone to see where any friend of yours was.

“Let me get your backpack for ya.”

Before you can decline, he slips it off your shoulders. “Really, I got it.”

He raises his brows crouching to look at your ankle, slipping on your backpack. “Your ankle is startin’ to swell.” He comes back up a little, “Put your arm around my neck.” One of his arms goes around your waist.

You do what he tells you, getting ready to limp by his side to the nurse. He sweeps you off your feet, literally.

Staring at him in shock, he just keeps walking like he does this every day for people.

The guys in his group are waving at you and you give them a shy wave back. The girls on the other hand, look like they want him to drop you.

“You don’t have to do this.”

“I know, I want to.”

“Why?” _Just accept it, jeez._

“’Cause you needed help, but you wouldn’t admit it.” He looks you in the eyes and you just about melt.

“Well, thank you.”

“Mhm. I’m Dean by the way.”

“(Y/N).”

“Nice to meet ya.” Dean states with a grin.

“Likewise.”

“You catch the bus all the time?”

“Um, when a friend of mine is available they drop me off at home. They don’t like me riding the bus too much.”

“I can see why. Nowadays it’s hard to stay safe sometimes.” He adjusts his arms and somehow you seem closer. “You have pepper spray or somethin’?”

“Um, no. I know that sounds bad…” You start to play with his collar.

“Why don’t you have any?” Dean sounds genuinely concerned.

“I just never thought to. Should I get some?”

“Definitely.”

When you two get to the nurse’s office, Dean crouches a little and has you open the door. Thank goodness, her door is open.

“Oh, what happened?” Nurse Nicole pops out of her seat.

“I fell and I think my ankle is sprained. I wanted to see if you had a wrap or something.”

“Come to the back, I think I do.”

Dean carries you to the back setting you on the bed.

“Thank you.”

“Welcome.”

He sets your backpack on the chair and your about to open your mouth to wish him a farewell, when he sits next to you on the bed.

“It’s sweet of you to carry your girlfriend here.”

Dean chuckles. “We’re not together. I actually just met her.”

_I wish._

“That’s very sweet of you. I look at couples walking together on campus and some guys don’t even pick up a book for their girlfriend.”

“I couldn’t let her limp all the way here. It just wouldn’t’ve sat right with me. Are you single?” He directs the question towards you.

“Yes…”

Dean nods, watching the nurse set down a pink wrap.

“Alright Sweetie, time for the hardest part. We have to take your shoe off.”

You sigh. “We can’t just put it on there like this.”

“No, Ma’am. I’ll give you time to prepare because I have to get your ice.”

She walks out of the back room.

You’re quietly whining as Dean kneels on the ground in front of you. He reaches for your shoe.

“Wait, what are you doing?”

“Takin’ off your shoe.”

“She’s gonna do it.”

“If you start cussin’, I’d rather it be at me than her.” He takes your shoe in his hands. Dean starts to untie your converse, loosening up the string. “Ready?”

“Mhm.”

Slowly, he begins to slide the back down. He touches your ankle.

“Dean.” You moan, gripping the thin paper on the bed.

“I know, Sweetheart. I’m sorry.” He snatches the shoe off.

You bite your lip, knowing your face says it all.

He comes back up pulling your head against his chest. “I’m sorry. I didn’t wanna make it longer than I had to. Don’t hate me.”

You blow out a breath, thinking about him calling you “Sweetheart”. It’s obvious your priorities are straight.

“It’s fine. I don’t hate you.”

Dean sits back down beside you, but this time his arm is around your shoulders.

“You ever sprained anything before?”

“Yeah, my other ankle, but it didn’t hurt this bad.” Yes, you’re in pain, but Dean, aka Green-Eyed Cowboy, was with you. _Amanda is not going to believe this._

“You fell kinda weird.”

“I was trying not to go face first in the concrete.”

“Speakin’ of that, you’re gonna feel that in your arm tomorrow.”

“Yeah…”

The nurse comes back in with a zip-lock of ice.

“I see the shoe is gone.”

“He took it off.”

Nicole looks back at Dean with a raised brow and he just shrugs with a smile.

As she starts to wrap it, Dean moves his arm from your shoulders to behind you with his hand by the hip that not connected with his. He’s watching what she’s doing and anytime you make a noise, you’ll feel his thumb on your hoodie.

Finished with the deed, she sends you on your way.

Outside of her office, you take out your phone.

“(Y/N)?”

“Hm?”

“I know this may seem like I’m up to no good but, can I take you home?”

_Did I hear that right?_

“Take me home?”

“Yeah. I’m just not comfortable lettin’ you get on the bus with that.” Even though he’s coming off shy, you know he’s confident as hell.

“Um, yeah. You can? You’ve already helped me out a lot. Are you sure?” He put your backpack on himself again. You were actually about to call for a ride.

“Positive.” He picks you up again.

It’s probably going to take you hours to tell Amanda this story because you know it will be filled with so many squeals.

On the way to the car, there’s no conversation except the one in your head.

He sets you down beside an old school car and opens the door for you.

_This is nice._

When he gets into the car you tell him the name of the apartments you live in and he knows exactly where it is.

You’re just basking in this time, enjoying the low set music volume in the car, and Dean’s tapping along.

“Could I ask you somethin’?”

“Yes.” You might’ve sounded dazed.

He huffs licking his lips, stopping at a red light. “Is it my legs that make me look like a cowboy?”

“Oh my god…” You whisper. _How the hell does he know about the name?_ “Yes? Sorry, we don’t mean any offence by it.”

Dean laughs, hitting the steering wheel. “No, I love it. I think it’s awesome. I’ve seen you around. Like that time, you almost fell down the stairs with your friend. She said the name a little too loud.”

“Whew, shit. You scared me for a second. She does talk too loud sometimes.”

“Wanna know your name?”

“I have a name?”

“Yeah.”

 _Amanda is about to plan a funeral because this has to be heaven._ “What is it?”

“Hoodie.”

“Hoodie?”

“Hoodie.” He looks completely satisfied.

“Why Hoodie?” You ask slowly.

“’Cause every time I see you, you got a hoodie on.”

_Duh, (Y/N). It’s all you wear to school._

“Seems appropriate.”

“I know right?”

Dean pulls into your apartment place, going to the complex you tell him to.

“Um, can you help me to my apartment?”

“Yeah.” He says happily.

You live on the second floor, so you’ll be able to hop up the steps with his help.

He wraps his arm around your waist and laughs along with you as you hop up the steps.

You open your door, after releasing him.

“Can I have your number?” Dean asks, digging in his pocket.

“Of course.”

He hands his phone to you and you lean against your door frame, inserting it. You trade his phone for your backpack.

“Thank you, Dean.”

You watch him spread his legs, put a hand on his belt buckle, and has his other hand in the air like he was touching the brim of a hat.

“Anytime Ma’am.” He dips his head down along with his hand and you’re fighting a very ugly laugh that wants to come out.

It ends up coming out. _Ahhh! He’s so cute!_

“Bye, Green-Eyed Cowboy.”

“Bye, Hoodie.” He turns and starts going down the steps.

You’re not even three limps from the door when there’s a knock. Opening it, you stand stock still when a kiss gets planted on your cheek.

“Bye.” He winks at you.

“Bye…” You say on a dreamy sigh.

He’s long gone by the time you close your door.

_Amanda better be good at funeral planning…_

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


	2. Chapter 2

You were sliding on a burgundy hoodie, getting ready for Dean to come over.

It was a mutual decision to not go out on a date date. So, Dean was coming over for the date. It would be more of just hanging out than a traditional date. Which is a relief because you don’t have to dress up. It wasn’t really your thing.

You had a brace on your ankle that you were advised to wear as long as your ankle was hurting.

So, you’ve been walking, just not as fast as you’d like.

You were turning on the TV when there’s a thud at the door.

Frowning, you look through the peep hole spotting Dean with his hands full.

“Howdy.” He says, when the door is full open.

“Howdy.” You return giggling, moving out of the way.

Dean walks in with two pizzas and a bag with two two-liter sodas in it. Not to mention he was wet.

You didn’t even know it was raining.

“I don’t wanna get your stuff wet, so do you have somewhere I can put my hoodie.”

You take the pizzas and bag. “You can put it in the dryer.”

“Oh, hell yeah. Where is it?”

“Go through the kitchen and it should be on the right.”

Dean starts his way to the kitchen and you set everything on the couch. You walk into the kitchen to see him pulling off his hoodie. His shirt comes off with it.

“Hate it when that happens.” He says, opening the dryer.

You’re getting down some cups and end up hitting some with the back of your hand.

“Shit.” You whisper, getting down to pick them up.

_Get ahold of yourself!_

It’s good thing they’re all plastic.

When you rise back up to put them in the sink, Dean’s looking at you.

“Do you have ranch?”

He still had the shirt in his hand.

“Yes… Why do you need ranch?”

“For my pizza.” You must’ve frowned because he starts laughing. “You’ve never dipped your pizza in ranch?”

“No…”

“You gotta try it.”

Slipping on the shirt, he opens the fridge.

Ranch and cups in hand you both head to the living room.

“I got two different drinks. You can have one to yourself or we can share. Whatever you wanna do? The same goes for the pizza.”

“Let's share.” You watch as Dean opens both boxes.

One cheese and the other was meat lovers.

_Have meh heart._

He gets up, heading to the kitchen. While he's in the kitchen, you open the sodas. A sprite and a coke.

“Sprite or coke?” You ask as he comes back with paper towels.

“Coke please.”

Pouring him his, he sits back down on the floor beside you grabbing the ranch. You pour sprite for yourself.

“Here we go. If you don't like it I give you permission to… pinch me. But not my nipples.”

When you laugh, he smirks a little.

Dean takes a paper towel and hands over a meat lovers slice to you with some ranch on it. He waits patiently for you to take a bite.

You want to smile so bad. But you know if you do, it’ll be one of those weird you might be insane ones. You do have to look away from him though, it's hard enough not melt from his gaze.

Taking a bite, you frown a bit.

“Oh no, you don't like it.”

“No.” You cover your mouth. “No, I do like it, I just wasn't expecting to.”

“I know what's good girl.” He says, ripping off one of the lids.

He puts two different ranch dipping areas on it. You dip your slice.

You eat in semi silence, the TV was still on.

Every couple of bites you would look at Dean. He has some ranch on his cheek.

_Wipe it._

“What's your last name?”

He looks at you. “Winchester. Yours?” You grab a paper towel, wiping his cheek. “Thanks.”

“(Y/L/N). It fits you. Dean Winchester.”

“My name almost was Henry.”

“Really?”

“Yep. Would've been Henry Ross Winchester, but my mom was like, “hell no”. And that is how I became Dean Ross Winchester. I'm glad she said, “hell no”.”

You cover your mouth again. “Do you have any siblings?”

“Yes. I have a little brother named, Sam. What about you?”

You shake your head. “Only child.”

“You ever get bored by yourself growin’ up?” He takes a sip of coke.

“Um, when my parents were busy I guess, but, um, I don't know what it's like to have a sibling so I can't really say.”

“They can be a pain in the ass sometimes.” Dean states honestly. “In a good way.”

“There's a good way?”

“Yeah. This is just from my experience as an older brother. When he was younger he loved to follow me around. Couldn't do anything without him wantin’ to tag along. Had to share my stuff with him. Sucked because if he broke it, then my dad would just say I shouldn't have gave it to him, but he's the one that made me in the first place. But I also love him. It's like there's some type of unspoken promise of I'll be there whenever you need me. He’d automatically come to me when he had problems and he still does. Anybody hurt him that's an automatic you have to deal with me. All he has to do is tell me. You get so attached to them, it's like they're your kid in a way. I love bein’ a big brother because it allows me to be a role model for him to look up to and it helps me stay on track because I know there’s someone watchin’ me that will take to heart the actions I do.”

_Aww, he just got even more perfect…_

“That's so sweet.” You weren't going to say that, but it's out now.

“I'm a big family man. Love ‘em all to death.”

“That's a good thing. Number one supporters should be your family.”

“Mhm.” He starts on another slice.

Almost done with the slice, he asks. “What's the first thing you noticed about me?”

“Um, your lips?”

“Ooo saucy.” He winks. “Why?”

_Don't do this._

“You really wanna know?”

“Yeah, why not?”

“They're full. They look soft all the time. Like you’re ready to-“

_Can't say that._

“Ready to what?”

“Uh, ready to… um. No, ‘cause then I’ll seem weird.”

“I like weird.” He's smiling at you like he knows what you're going to say.

You sigh. “Like you’re ready to make out.”

“You thought about makin’ out with me?”

“Yes…”

Dean wipes his hands and drinks some coke. “If it were to happen, how do you think it’ll be?”

“Making out with you?”

“Yeah.”

You start picking at some meat on your pizza. “Slow?”

Dean nods, smile still intact. “The first thing I noticed about you was your smile.”

“I hate my smile.”

“Why?”

“‘Cause it looks goofy half the time.”

“I think it's cute, but if you don't like that you won't like what I'm about to say next.”

“And what is that?”

“The second thing I noticed was your laugh. And I think you snorted.”

“No! Oh my god, Dean stop. That's so embarrassing.”

He laughs. “I'm just tellin’ the truth.” Looking towards your TV set, his eyes scan it. “Is that a PS4?”

“Yeah, wanna play it?”

“You have co-op games?”

“Mhm.”

“Then yeah.”

You change the TV over to the channel it should be on. Taking the controllers off the stand, you give him one.

When the screen is fully up Dean takes your controller, going to your friends list. He beings searching for a name and once he finds it, he sends them a friend request. After, he hands it back.

A handful of games online games later, Dean proposes that he could beat you in a 1v1, you told him that you highly doubted that. Now, you both were running around the map playing gun game.

As you shoot him in the back with the Haymaker and progress to the next weapon, Dean is trying to knock the controller out of your hand.

“Ah, don’t cheat.”

“It’s not cheatin’, it’s strategizin’.”

He attempts to melee you, but you shoot him in the face.

“What the hell?...” He whispers.

“I tried to tell you.”

The game progresses and you have to punch him, which is the very last kill you have to make in order to win.

Your controller is taken away and Dean scoots away with both.

“Give me my controller so I can murder you.”

“Come get it if you want It.” He kills you.

He’s only a few weapons away from you. Around the pizza lid you go, he takes the controller and hides it under his shirt. Your person was currently running into a wall.

As you reach for the bottom of the shirt, excited; he traps you in his arms. Still focused on the game.

You were against his chest and across his lap. As much as you wanted to live this moment to the fullest, you couldn’t because you really wanted to beat him.

Grabbing your controller and knocking his out of his hands, you punch him before he could knife you.

“Yes!” You throw your arms up, sliding off his lap.

Dean grabs some pizza he wasn’t finished eating.

“Whatcha gotta say now? Huh? You “strategized” and I still beat you.”

“Well, um, I’m gonna cry myself to sleep tonight.” He whispers, stuffing the crust in his mouth. “Then I’m gonna dropout and strive to do better.”

“And after you strive to do better?”

“I’m gonna find you and beat you at gun game fair and square.”

No longer able to be serious, you start laughing.

Dean pushes you over, resulting in you laughing harder.

You start to snort and can’t stop.

“Ow my stomach, I can’t.” When you peek at Dean he had his phone out smiling. “No! Don’t fuckin’ record me.” You laugh, weakly grabbing his wrist.

“I won’t show anyone else.” He says.

“Hahaow do I know that?”

“’Cause you can take my word for it.”

You fully sit up, pulling his arm down. “No, I know that I’m snorting on that.”

“It’s cute.”

“Delete it.”

“Can’t do that.”

“Why?”

“’Cause I don’t want to.”

Trying to pry his hand open for the phone, he pulls you closer amused.

“Open your hand.”

“You got it.”

Huffing, you attempt to pull his arm, but since he’s stronger than you; it’s not going anywhere.

“Can I please keep it?”

Looking up, you realize his face is a lot closer than it was before. His hand squeezes your waist. Slowly, you release his hand, feeling your face heat up.

“You can keep it.”

“Thank you.” He says softly.

You nod, freaking out internally.

Dean’s hand slips from your waist to your hand.

_Does my breath stink? It can’t, we were just talking. What if he’s being nice about it? Nononono. I have to check. What if I ruin the moment? I can’t._

Moving forward, Dean’s lips connect gently with yours.

Just like you imagined, it’s slow and his lips are soft.

You take your hand out of his to redirect it to the back of his head. Hearing something hit the floor, you ignore it as Dean drags you onto his legs, wrapping you up in his arms. Most of your French kissing experiences are bad, but he’s not trying to shove his tongue down your throat.

He has a hand on your thigh that you grab and move to your ass. Dean squeezes and caresses it.

You wish you could straddle him, but your ankle wouldn’t allow that position.

A phone goes off and he pulls back sighing. Dean picks up his phone from where he dropped it.

“Hello?”

You drop your hand from behind his head, placing it in between you two.

“I’m with (Y/N)… Yeah… Yeah, I’m still comin’… It’s not that late…” Dean pulls the phone away from his face, grimacing slightly. “Just gimme a bit… Alright.” He hangs up. “That was Cas. He has a test tomorrow and I told him I would help him study for it.”

You nod, moving off of him. “You should get going.” Taking your leftover pizza, soda, and the ranch bottle, you go into the kitchen, storing them in the refrigerator. You hear him coming towards the kitchen.

It was going on 9:30 right now and while that may seem “early” for other people, when you have a test or something the next day, or a job, time cannot and should not be wasted.

He throws away the pizza lid and the other half of the pizza box, after setting his coke on the counter.

“Come here.”

Slightly limping towards him, he meets you halfway, picking you up to put you on an empty space on the counter. Dean wastes no time connecting his lips to yours.

You place a hand on his jaw and your other on his shoulder.

He gently tugs your bottom lip. “How soon can I come back over?” Dean whispers against your lips.

“When you want to?” You whisper back; mind total mush.

Dean pulls you off the counter, carefully setting you on your feet. “I’ll make sure to get with you before headin’ over.” He grabs the coke and walks out of the kitchen towards the front door.

Front door open, he pokes his head out. “It stopped rainin’.”

You look out when he steps outside of the door.

“I’ll be seein’ ya. Shoot me a call or text, okay?”

You nod, allowing him to kiss you one last time before he heads to the stairs.

Shutting the door, you sigh thinking about how great the night went. You make your way over to the cups on the floor, picking them up.

As you’re washing all the cups out, you start to feel giddy over the thought of Dean’s playfulness.

Currently, there is a video of you laughing so hard that you’re snorting on someone’s phone and you’re happy with that. It’s so mushy, but you can just imagine him having a bad day and looking at that video to cheer himself up.

It was just one date, but it’s still a nice thought to have.

You know it’s late, but there’s still excitement in you and you need to wash clothes. After stuffing clothing into the washer, you set up on the couch and start playing multiplayer C.O.D..

A crap load of games later, you start to feel sleepy. Shutting off your PS4, you straighten up the living room and head into the laundry area.

Opening the dryer, you turn around to open the washer. Handful of clothes in hand, you’re just about to throw them in the dryer when you see something black inside. Whatever it is, you set it on top of the dryer until it is filled with the wet clothing.

Dryer started, you take the item off the dryer, flipping it the right way. It’s Dean’s hoodie…

Unconsciously, you hold it against your chest, making your way back into the living room to get your phone.

Not thinking of how late it is, you have the phone up to your ear, waiting on him to pick up.

 _ **“Hello?”**_ He sounds tired.

“Oh, I’m sorry.”

_**“It’s fine. What’s up, Sweetheart?”** _

“Um, you left your hoodie here.”

 _ **“Keep it. Next time I see you, you better be wearin’ it.”**_ Dean says without skipping a beat.

You pull the phone away from your head, in case a noise come out of your silent squeal. “I’ll make sure I am.” You say, hugging the hoodie tighter.

_**“Alright, I’ll talk to ya later. Cas, is givin’ me the stank eye.”** _

“Okay, bye.”

 _ **“Bye, Sweetheart.”**_ He hangs up.

You’re totally gonna flaunt his hoodie around school. You can see it now, it’ll probably be the only one you’ll ever wear now.

How cowboy’s, or country boys, would take off their hats and put it on the girls’ head; him leaving his hoodie here for you to wear is like the equivalent.

He’s your modern-day city cowboy and you’ll proudly milk every inch of that thought.

**Notes for the Chapter:**

> Comments and kudos are always welcomed!!! <3


End file.
